Electrophilic carbocyclization reactions of 2-(2-alkynylphenyl)amino-1,4-naphthoquinones

Organic & Biomolecular Chemistry
Chang-You Sie, Che-Ping Chuang

Abstract

An efficient Ag(i)-catalyzed method for the synthesis of 5H-benzo[b]naphtho[2,3-f]azepine-6,11-diones from 2-(2-ethynylphenyl)amino substituted 1,4-naphthoquinones has been developed. In this transformation new C-C bond formation occurred regioselectively via a 7-endo-dig cyclization. The related 13-iodine substituted benzazepine derivatives could also be produced exclusively by the I2-induced carbocyclization reaction of 2-(2-alkynylphenyl)amino substituted 1,4-naphthoquinones. This process has advantages such as mild reaction conditions and tolerance of a broad range of functional groups.

References

Jul 4, 2001·Journal of Natural Products·M H ChavesN F Roque
May 13, 2004·Chemical Reviews·Branko Stanovnik, Jurij Svete
Jul 12, 2005·Bioorganic & Medicinal Chemistry Letters·Brent R CoppScott G Franzblau
Dec 27, 2005·Bioorganic & Medicinal Chemistry·José M Miguel del CorralArturo San Feliciano
Mar 11, 2008·Journal of Natural Products·Michael N Gandy, Matthew J Piggott
Sep 1, 2009·Bioorganic & Medicinal Chemistry Letters·Waya S PhutdhawongThongchai Taechowisan
May 25, 2010·The Journal of Organic Chemistry·Chunhui JiangZhu-Jun Yao
May 31, 2012·Archives of Pharmacal Research·Weerachai PhutdhawongWaya S Phutdhawong
Apr 1, 2014·Organic & Biomolecular Chemistry·Kommuru GouthamGalla V Karunakar
Apr 22, 2014·The Journal of Organic Chemistry·Wouter DebrouwerChristian V Stevens
May 1, 2015·Organic & Biomolecular Chemistry·Haruki MizoguchiHiroki Oguri
Oct 16, 2015·The Journal of Organic Chemistry·Kommuru GouthamGalla V Karunakar
Feb 17, 2017·Organic & Biomolecular Chemistry·Yi-Chen ChengChe-Ping Chuang

❮ Previous
Next ❯

Citations


❮ Previous
Next ❯

Methods Mentioned

BETA
column chromatography
NMR

Related Concepts

Related Feeds

Antibodies: Agglutination

Antibody-mediated agglutination is the clumping of cells in the presence of antibody, which binds multiple cells together. This enhances the clearance of pathogens. Find the latest research on antibody-mediated agglutination here.